US Road Running - Winding Cypress

APR
18
2026
Set sail for a pirate-themed run at Eagle Lakes Community Park in Naples. Choose from a 5K, 10K, or Half Marathon on asphalt out-and-back courses. All finishers get a themed medal, and costumes are encouraged for a chance to win an award.
Sat 18 Apr 2026
Half Marathon 10 kilometers 5 kilometers

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Event Overview

The Pirate 5K, 10K, and Half Marathon takes place at Eagle Lakes Community Park in Naples, Florida.

Distances and Courses

The event offers three race distances:

  • 5K (3.11 miles)
  • 10K (6.22 miles)
  • Half Marathon (13.1 miles)

All courses are on asphalt and follow an out-and-back format. The 5K and 10K share a 1.56-mile out-and-back segment; the 5K completes it once, while the 10K completes it twice. The Half Marathon uses a 1.64-mile out-and-back segment, completing it four times. There is an overall course time limit of 3 hours and 30 minutes.

Event Details

The start line is by the tennis courts at Eagle Lakes Community Park. Bathrooms are located in a pavilion near the start. Packet pickup begins 30 minutes before the race and ends 10 minutes before the start. Registration is required online in advance; there is no on-site registration.

Additional Notes

All finishers receive a themed medal. While optional, runners are encouraged to wear costumes; there is a best costume award presented at the start of the race, and a group photo is taken for each event. This race earns points for the US Road Running Race Series. Visit the organization's website for the most recent information.

Half Marathon
Half Marathon
10 km
10k
5 km